Furfural
IUPAC name	Furan-2-carbaldehyde
Other names	furfural, furan-2-carboxaldehyde, fural, furfuraldehyde, pyromucic aldehyde
Identifiers
CAS number	[98-01-1]
PubChem	7362
SMILES	O=Cc1ccco1
InChI	1/C5H4O2/c6-4-5-2-1-3-7-5/h1-4H
Properties
Molecular formula	C5H4O2
Molar mass	96. IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to PubChem is a Database of chemical Molecules The system is maintained by the National Center for Biotechnology Information (NCBI a component The IUPAC International Chemical Identifier ( InChI, pronounced "INchee" is a textual Identifier for Chemical substances designed to provide a A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Molar mass, symbol M, is the Mass of one mole of a substance ( Chemical element or Chemical compound) 08 g mol-1
Appearance	Colorless oil
Density	1. The density of a material is defined as its Mass per unit Volume: \rho = \frac{m}{V} Different materials usually have different 16 g/mL liquid
Melting point	-36. The melting point of a solid is the temperature range at which it changes state from solid to Liquid. 5 °C
Boiling point	161. The boiling point of a liquid is the temperature at which the Vapor pressure of the liquid equals the environmental pressure surrounding the liquid 7 °C
Hazards
Flash point	62 °C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

The chemical compound furfural is an industrial chemical derived from a variety of agricultural byproducts, including corncobs, oat and wheat bran, and sawdust. The flash point of a flammable liquid is the lowest Temperature at which it can form an ignitable mixture in air In Chemistry, the standard state of a material is its state at 1 bar (100 Kilopascals exactly A chemical compound is a substance consisting of two or more different elements chemically bonded together in a fixed proportion by Mass. Agriculture refers to the production of goods through the growing of plants and fungi and the raising of domesticated Animals The study of agriculture Maize (ˈmeɪz ( Zea mays L. ssp mays) known as corn in some countries is a cereal grain domesticated in Mesoamerica Oats redirects here It may mean either the common cereal oat discussed here or any cultivated or wild species of the Genus Avena. Wheat ( Triticum spp is a worldwide cultivated grass from the Levant area of the Middle East. Bran is the hard outer layer of Grain and consists of combined Aleurone and Pericarp. Sawdust is composed of fine particles of Wood. This material is produced from cutting with a Saw, hence its name The name furfural comes from the Latin word furfur, meaning bran, referring to its usual source. Latin ( lingua Latīna, laˈtiːna is an Italic language, historically spoken in Latium and Ancient Rome.

Furfural is an aromatic aldehyde, with the ring structure shown at right. An aldehyde is an organic compound containing a terminal Carbonyl group. Its chemical formula is C₅ H₄ O₂. A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Carbon (kɑɹbən is a Chemical element with the symbol C and its Atomic number is 6 Hydrogen (ˈhaɪdrədʒən is the Chemical element with Atomic number 1 Oxygen (from the Greek roots ὀξύς (oxys (acid literally "sharp" from the taste of acids and -γενής (-genēs (producer literally begetteris the In its pure state, it is a colorless oily liquid with the odor of almonds, but upon exposure to air it quickly becomes yellow. The Almond ( Prunus dulcis, syn Prunus amygdalus Batsch Amygdalus communis L

Contents 1 History 2 Properties 3 Production 4 Uses 5 Safety 6 References

History

Furfural was first isolated in 1832 by the German chemist Johann Wolfgang Döbereiner, who formed a very small quantity of it as a byproduct of formic acid synthesis. Germany, officially the Federal Republic of Germany ( ˈbʊndəsʁepuˌbliːk ˈdɔʏtʃlant is a Country in Central Europe. A chemist is a Scientist trained in the Science of Chemistry. Johann Wolfgang Döbereiner ( December 13, 1780 &ndash March 24, 1849) was a German chemist who is best known for Formic acid (systematically called methanoic acid) is the simplest Carboxylic acid. ^[1] At the time, formic acid was formed by the distillation of dead ants, and Döbereiner's ant bodies probably contained some plant matter. Distillation is a method of separating Mixtures based on differences in their volatilities in a boiling liquid mixture Ants are social Insects of the family Formicidae and along with the related families of Wasps and Bees belong to the order In 1840, the Scottish chemist John Stenhouse found that the same chemical could be produced by distilling a wide variety of crop materials, including corn, oats, bran, and sawdust, with aqueous sulfuric acid, and he determined that this chemical had an empirical formula of C₅H₄O₂. Scotland ( Gaelic: Alba) is a Country in northwest Europethat occupies the northern third of the island of Great Britain. John Stenhouse ( October 31, 1809 &ndash December 31, 1880) was a Scottish Chemist. Sulfuric (or sulphuric acid, H 2 S[[oxygen O]]4 is a strong Mineral acid. Use in chemistry In Chemistry, the empirical formula of a Chemical compound is a simple expression of the relative number of each type of Atom In 1901, the German chemist Carl Harries deduced furfural's structure. Carl Dietrich Harries ( August 5[[ 866]] - November 3 1923) was a German Chemist.

Except for occasional use in perfume, furfural remained a relatively obscure chemical until 1922, when the Quaker Oats Company began mass-producing it from oat hulls. Perfume is a mixture of fragrant Essential oils and Aroma compounds Fixatives and Solvents used to give the human body animals objects and living The Quaker Oats Company is an American food conglomerate based in Chicago. Today, furfural is still produced from agricultural byproducts like sugarcane bagasse and corn cobs. Bagasse (sometimes spelled bagass) is the Biomass remaining after Sugarcane or Sorghum stalks are crushed to extract their juice and is Maize (ˈmeɪz ( Zea mays L. ssp mays) known as corn in some countries is a cereal grain domesticated in Mesoamerica

Properties

Furfural's physical properties are summarized in the table at right. Furfural dissolves readily in most polar organic solvents, but is only slightly soluble in either water or alkanes. Organic chemistry is a discipline within Chemistry which involves the scientific study of the structure properties composition reactions, and preparation Water is a common Chemical substance that is essential for the survival of all known forms of Life. Alkanes, also known as Paraffins are Chemical compounds that consist only of the elements Carbon (C and Hydrogen (H (i

Chemically, furfural participates in the same kinds of reactions as other aldehydes and other aromatic compounds. The aromatic stability of furfural is not as great as in benzene, and furfural participates in hydrogenation and other addition reactions more readily than many other aromatics. Benzene, or benzol, is an organic Chemical compound and a known Carcinogen with the molecular formula C 6 H 6 Hydrogenation is the Chemical reaction that results in addition of Hydrogen (H2 An addition reaction, in Chemistry, is in its simplest terms an Organic reaction where two or more molecules combine to form a larger one

When heated above 250 °C, furfural decomposes into furan and carbon monoxide, sometimes explosively. Furan, also known as furane and furfuran, is a heterocyclic Organic compound. Carbon monoxide, with the chemical formula CO is a colorless odorless tasteless yet highly toxic Gas.

When heated in the presence of acids, furfural irreversibly solidifies into a hard thermosetting resin. Resin, not to be confused with Rosin, is a Hydrocarbon Secretion of many Plants particularly coniferous trees.

Production

Many plant materials contain the polysaccharide hemicellulose, a polymer of sugars containing five carbon atoms each. Polysaccharides are relatively complex Carbohydrates They are Polymers made up of many Monosaccharides joined together by Glycosidic bonds A hemicellulose can be any of several Heteropolymers (matrix polysaccharides present in almost all plant cell walls along with Cellulose. A polymer is a large Molecule ( Macromolecule) composed of repeating Structural units typically connected by Covalent Chemical bonds Sugar is a class of edible Crystalline substances mainly Sucrose, Lactose, and Fructose. When heated with sulfuric acid, hemicellulose undergoes hydrolysis to yield these sugars, principally xylose. Hydrolysis is a Chemical reaction during which one or more water molecules are split into hydrogen and hydroxide ions which may go on to participate in further reactions Xylose or wood sugar is an Aldopentose &mdash a Monosaccharide containing five Carbon Atoms and including an Aldehyde Functional Under the same conditions of heat and acid, xylose and other five carbon sugars undergo dehydration, losing three water molecules to become furfural:

C₅H₁₀O₅ → C₅H₄O₂ + 3 H₂O

For crop residue feedstocks, about 10% of the mass of the original plant matter can be recovered as furfural. Xylose or wood sugar is an Aldopentose &mdash a Monosaccharide containing five Carbon Atoms and including an Aldehyde Functional Water is a common Chemical substance that is essential for the survival of all known forms of Life. Furfural and water evaporate together from the reaction mixture, and separate upon condensation.

Global total capacity of production is about 450,000 ton. China is the biggest supplier of this product and they have about a half of global capacity. China ( Wade-Giles ( Mandarin) Chung¹kuo² is a cultural region, an ancient Civilization, and depending on perspective a National

In the laboratory, synthesis of furfural from corn cobs takes place by reflux with dilute sulfuric acid ^[2]. This article is about using reflux in chemical engineering and chemistry Sulfuric (or sulphuric acid, H 2 S[[oxygen O]]4 is a strong Mineral acid.

Uses

Furfural is used as a solvent in petrochemical refining to extract dienes (which are used to make synthetic rubber) from other hydrocarbons. A solvent is a liquid or gas that dissolves a solid liquid or gaseous Solute, resulting in a Solution. Petrochemicals are chemical products made from raw materials of Petroleum or other Hydrocarbon origin Refining (also called affining) is the process of Purification of a substance. Dienes or diolefins are Hydrocarbons which contain two double bonds. In Organic chemistry, a hydrocarbon is an Organic compound consisting entirely of Hydrogen and Carbon.

Furfural, as well as its derivative furfuryl alcohol, can be used either by themselves or in together with phenol, acetone, or urea to make solid resins. Furfuryl alcohol, also called 2-furylmethanol or 2-furancarbinol is an Organic compound containing a Furan substitited with a Hydroxymethyl group Phenol, is a toxic colourless Crystalline Solid with a sweet tarry odor commonly referred to as a "hospital smell" Acetone (also known as propanone, dimethyl ketone, 2-propanone, propan-2-one and β-ketopropane) is a colorless mobile flammable Urea is an Organic compound with the Chemical formula ( N[[hydrogen H]]22 C[[oxygen O]] Such resins are used in making fiberglass, some aircraft components, and automotive brakes. Fiberglass (also called fibreglass and glass fibre see Spelling differences) is material made from extremely fine Fibers of Glass. A brake is a device for slowing or stopping the motion of a Machine or Vehicle, or alternatively a device to restrain it from starting to move again

Furfural is also used as a chemical intermediate in the production of the solvents furan and tetrahydrofuran. Furan, also known as furane and furfuran, is a heterocyclic Organic compound. "THF" redirects here For other uses see THF (disambiguation. Hydroxymethylfurfural has been identified in a wide variety of heat processed foods. Hydroxymethylfurfural, HMF or 5-(Hydroxymethylfurfural is an Aldehyde and a Furan compound formed during the Thermal decomposition

Safety

When ingested or inhaled, furfural can cause intoxication, including euphoria, headache, dizziness, nausea, and eventual unconsciousness and death due to respiratory failure. Intoxication is the state of being affected by one or more psychoactive drugs. Euphoria is a medically recognized emotional state related to Pleasure and Happiness. A headache ( cephalalgia in medical terminology is a condition of pain in the Head; sometimes Neck or upper back pain may also be interpreted Many different terms are often used to describe what is collectively known as dizziness. Nausea ( Latin: Nausea, Greek:, " Sea-sickness " also called wamble) is the sensation of unease and discomfort Contact with furfural irritates the skin and respiratory tract and can cause the lungs to fill with fluid. The skin is the outer covering of living tissue of an animal (or plant In humans the respiratory tract is the part of the Anatomy that has to do with the process of respiration. lung is the essential Respiration organ in air-breathing Animals including most Tetrapods a few Fish and a few Snails The most primitive

Chronic skin exposure can lead to a skin allergy to the substance, as well as an unusual susceptibility to sunburn. Allergy is a disorder of the Immune system often also referred to as Atopy. A sunburn is a burn to living tissue such as Skin produced by overexposure to Ultraviolet (UV radiation commonly from the Sun 's rays In toxicity studies, furfural has led to tumors, mutations, and liver and kidney damage in animals. See also Cancer A tumor or tumour is the name for a swelling or lesion formed by an abnormal growth of cells (termed neoplastic In biology mutations are changes to the Nucleotide sequence of the Genetic material of an organism The liver is a vital organ in the human body and is present in Vertebrates and some other animals The kidneys are complicated organs that have numerous biological roles

References

1. ^ J. W. Döbereiner (1832). "Ueber die medicinische und chemische Anwendung und die vortheilhafte Darstellung der Ameisensäure". Berichte der deutschen chemischen Gesellschaft 3 (2): 141-146. doi:10.1002/jlac.18320030206. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document.  
2. ^ Roger Adams and V. Voorhees (1921). "Furfural". Org. Synth. 1: 49; Coll. Organic Syntheses is a Scientific journal that since 1921 has provided the Chemistry community with annual collections of detailed and checked procedures Vol. 1: 280.  

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